COX-1/cyclooxygenase-1 (IC50 = 3.2μM)

(-)-Epicatechin has an IC50 of 3.2 μM and >95% inhibitory action against cyclooxygenase-1 (COX-1) at 70 μg/mL [1]. (-)-Epicatechin NF-blocks the nuclear localization of the κB p65 subunit, which prevents IL-1β-induced iNOS production. It has been demonstrated that the addition of IL-1β causes (-)-epicatechin to burst and limit insulin release in RINm5F cells. Furthermore, it was proven that (-)-epicatechin was swellable. It increases the capacity of (-)-epicatechin to prevent NF-κB from binding to DNA in these cells by suppressing the growth of Jurkat T cells and Hodgkin's positioning cells. Combining 20 μM Panaxadiol with 150, 200, or 250 μM (-)-Epicatechin inhibited proliferation in human rectal cancer HCT-116 cells by 51%, 97%, and 95%, respectively. The swapped cell fluorescence levels increased by 11.9%, 16.6%, and 25.8%, as shown by Annexin V/PI staining [2].

The animals were given water (vehicle) or 1 mg/kg of (-)-epicatechin via wall gavage twice a day. Over the course of 15 days, the exercise group used a treadmill. Utilizing (-)-epicatechin can boost fatigue resistance during in situ visits by around 30% and improve treadmill performance by approximately 50% [3].

Experimental design and approach[2]
A between-subjects design was used to determine the effects of (–)-epicatechin on the hindlimb muscles of 1-year-old mice. This age was selected because it has been shown that by 1 year there are decreases in exercise capacity when compared to young (4–6 months) mice (Leick et al. 2010). All animals performed an incremental treadmill test and were then subsequently randomized into four groups: (1) water, (2) water–exercise (W-Ex), (3) (–)-epicatechin ((–)-Epi), and (4) (–)-epicatechin–exercise ((–)-Epi-Ex). Groups 2 and 4 performed exercise on a rodent treadmill Monday through Friday during the study period. On the day after the final training session, all mice performed an incremental treadmill test. Forty-eight hours following the treadmill test, the mice were killed. The quadriceps femoris, extensor digitorum longus (EDL), and plantaris muscles for all groups were harvested and used for morphometric, biochemical, isolated-muscle preparation, and molecular analyses.

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(–)-Epicatechin administration[3]
Mice in the (–)-epicatechin groups 3 and 4 were given 1.0 mg (kg body mass)−1 twice a day (morning and evening) for 15 consecutive days, whereas animals in the control groups 1 and 2 received the vehicle (water). Both (–)-epicatechin and vehicle were administered via oral gavage.

Metabolism / Metabolites
Epicatechin has known human metabolites that include 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone and Phloroglucinol.

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A small quantitative clinical study with human subjects consuming 80 grams of procyanidin-rich chocolate containing 137 mg (470 μmol) (−)-epicatechin showed that blood (−)-epicatechin increased 12-fold over baseline levels to 257 ± 66 nmol/L after 2 hours and then declined to baseline levels in 8 out of the ten subjects after 6 hours, while it further increased in the remaining two individuals [39]. This suggests that there is a large heterogeneity regarding the half-life and metabolism of (−)-epicatechin in humans. Bioavailability of native (−)-epicatechin is therefore smaller than for vitamins C and E, with about ~1/200 and ~1/150 bioavailability, respectively. Given that most of the ingested (−)-epicatechin undergoes chemical modifications, the glucuronidated and methylated products likely play a key role for the biological effect in addition to the native compound.[2]

[1]. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.

[2]. Molecular Mechanisms and Therapeutic Effects of (-)-Epicatechin and Other Polyphenols in Cancer, Inflammation, Diabetes, and Neurodegeneration. Oxid Med Cell Longev. 2015;2015:181260.

[3]. (-)-Epicatechin enhances fatigue resistance and oxidative capacity in mouse muscle. J Physiol. 2011 Sep 15;589(Pt 18):4615-31.

(-)-epicatechin is a catechin with (2R,3R)-configuration. It has a role as an antioxidant. It is a polyphenol and a catechin. It is an enantiomer of a (+)-epicatechin.
Epicatechin has been used in trials studying the treatment of Pre-diabetes.
(-)-Epicatechin has been reported in Camellia sinensis, Cecropia hololeuca, and other organisms with data available.
An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.
See also: Crofelemer (monomer of); Bilberry (part of); Cat's Claw (part of) ... View More ...

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With recent insight into the mechanisms involved in diseases, such as cardiovascular disease, cancer, stroke, neurodegenerative diseases, and diabetes, more efficient modes of treatment are now being assessed. Traditional medicine including the use of natural products is widely practiced around the world, assuming that certain natural products contain the healing properties that may in fact have a preventative role in many of the diseases plaguing the human population. This paper reviews the biological effects of a group of natural compounds called polyphenols, including apigenin, epigallocatechin gallate, genistein, and (-)-epicatechin, with a focus on the latter. (-)-Epicatechin has several unique features responsible for a variety of its effects. One of these is its ability to interact with and neutralize reactive oxygen species (ROS) in the cell. (-)-Epicatechin also modulates cell signaling including the MAP kinase pathway, which is involved in cell proliferation. Mutations in this pathway are often associated with malignancies, and the use of (-)-epicatechin holds promise as a preventative agent and as an adjunct for chemotherapy and radiation therapy to improve outcome. This paper discusses the potential of some phenolic compounds to maintain, protect, and possibly reinstate health.[2]
The flavanol (-)-epicatechin, a component of cacao (cocoa), has been shown to have multiple health benefits in humans. Using 1-year-old male mice, we examined the effects of 15 days of (-)-epicatechin treatment and regular exercise on: (1) exercise performance, (2) muscle fatigue, (3) capillarity, and (4) mitochondrial biogenesis in mouse hindlimb and heart muscles. Twenty-five male mice (C57BL/6N) were randomized into four groups: (1) water, (2) water-exercise (W-Ex), (3) (-)-epicatechin ((-)-Epi), and (4) (-)-epicatechin-exercise ((-)-Epi-Ex). Animals received 1 mg kg(-1) of (-)-epicatechin or water (vehicle) via oral gavage (twice daily). Exercise groups underwent 15 days of treadmill exercise. Significant increases in treadmill performance (∼50%) and enhanced in situ muscle fatigue resistance (∼30%) were observed with (-)-epicatechin. Components of oxidative phosphorylation complexes, mitofilin, porin, nNOS, p-nNOS, and Tfam as well as mitochondrial volume and cristae abundance were significantly higher with (-)-epicatechin treatment for hindlimb and cardiac muscles than exercise alone. In addition, there were significant increases in skeletal muscle capillarity. The combination of (-)-epicatechin and exercise resulted in further increases in oxidative phosphorylation-complex proteins, mitofilin, porin and capillarity than (-)-epicatechin alone. These findings indicate that (-)-epicatechin alone or in combination with exercise induces an integrated response that includes structural and metabolic changes in skeletal and cardiac muscles resulting in greater endurance capacity. These results, therefore, warrant the further evaluation of the underlying mechanism of action of (-)-epicatechin and its potential clinical application as an exercise mimetic.[3]

C15H14O6

290.27

290.079

C, 62.07; H, 4.86; O, 33.07

490-46-0

(-)-Epicatechin gallate;1257-08-5;(+)-Epicatechin;35323-91-2;(±)-Epicatechin-13C3;1217780-28-3; 490-46-0

72276

White to light yellow solid powder

1.6±0.1 g/cm3

630.4±55.0 °C at 760 mmHg

240 °C (dec.)(lit.)

335.0±31.5 °C

0.0±1.9 mmHg at 25°C

1.742

0.49

5

6

1

21

364

2

C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

PFTAWBLQPZVEMU-UKRRQHHQSA-N

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

epi-Catechin; (-)-Epicatechin; (-)-Epicatechin; Epicatechin; 490-46-0; L-Epicatechin; Epicatechol; l-Acacatechin; (-)-Epicatechol; epi-Catechin; Epicatechin

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~344.51 mM)
H2O : ~2 mg/mL (~6.89 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)